


A Match Made In Arkham

by Esperata



Category: Batman: The Animated Series
Genre: Blind Date, Dinner Date, Ed Is Oblivious, Hattercrow (background), M/M
Language: English
Status: Completed
Published: 2020-05-28
Updated: 2020-05-30
Packaged: 2021-03-02 20:13:23
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,738
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24422572
Author URL: https://archiveofourown.org/users/Esperata/pseuds/Esperata
Summary: Riddler finds it unfathomable that Penguin hasn't found the partner of his dreams yet and so decides to set him up with someone. If only he can find someone worthy enough.
Relationships: Oswald Cobblepot/Edward Nygma
Comments: 66
Kudos: 124





	1. Chapter 1

It had started in the Iceberg Lounge with a drunken evening of exchanged tipsy compliments and uninhibited boastful bragging. Both three sheets to the wind and comfortably relaxed in each other’s company.

“But you!” Riddler declared with a flourish. “You. You’re the peak. The pinnacle. You’re an inspiration. And an aspiration. What more could anybody want?”

He flung an arm out with exaggerated emphasis to encompass the whole lounge and by extension Penguin’s empire in Gotham. The place was glittering like a jewel and if he hadn’t been feeling so sluggish he probably would have drawn some further comparison.

“Ah!” Oswald waved his own hand in a vaguely circling gesture that could have meant anything. “Someone to share it with my dear friend. Someone to share it with.”

As Edward blinked in momentary stunned silence, and Oswald continued to stare mournfully back at him, the idea suddenly blossomed in his mind. _He_ could find someone for Ozzie!

Of course at the time he’d merely stored the thought for later consideration. Subsequent events had not graced him with sufficient time to bring it out to re-examine it in the light of day. He’d had schemes to plan and plots to enact. So it wasn’t until he was temporarily ensconced within Arkham that he found himself at leisure to reconsider it.

Turning the idea around and around he found no flaw to the concept. Oswald was certainly deserving of a partner to share his highs and lows with. It was a mystery in fact that he hadn’t been snapped up already. Although when one considered the standards a prospective partner should have to meet, well, there weren’t that many people who could theoretically deserve Oswald.

Just off the top of his head, Ed struggled to think of any potential candidates. They would have to be highly intelligent of course. Sophisticated enough to appreciate the high-class interests Oswald enjoyed. A gifted conversationalist to entertain him. Attractive, naturally. While Edward understood that beauty was in the eye of the beholder, and Oswald might see things differently, if Ed were to pick someone for him then they had to possess jaw dropping good looks. People had to look at the pair of them and see Oswald’s glory reflected in his partner.

It would be preferable if they were capable of supporting him in his criminal activities to boot but Ed would concede that might be asking too much. He’d settle for finding an individual with a suitable easy going attitude to crime, which shouldn’t be hard in Gotham. But even with that concession Ed was struggling to think of how one would find such a person.

For himself he’d never really sought a long-time partner and simply took advantage of opportunities as they arose. He had never been too picky since he wouldn’t see them beyond the one encounter. In fact, until falling in with the Gotham rogues, he’d never even had any steady friendships. Now he would easily admit to Oswald being his closest dearest friend. He’d never had anyone he related to so easily as the Penguin.

The reminder of friendships brought his other two nearest acquaintances to mind and he grinned as he realised their expertise might be just what he required.

Jonathan Crane had been a professor of psychology. He would know how to interview suitable candidates to make sure they were up to standard. Ed would also admit that Jonathan was one of the few people he knew who almost matched his own intelligence so he wouldn’t need to worry about him overestimating other people’s mental attributes.

Jervis Tetch was attuned to the nature of romance and would have, for want of a better word, a _feel_ for potential matches. Whereas Ed would prefer to deal with the situation entirely rationally, he recognised emotions did not work that way. Jervis had the edge over him in that field. Plus he had the useful ability to mind control any prospective dates if things went south.

Luckily for him the pair of them had been incarcerated shortly before him, caught by the Batman as they combined their talents on a joint heist. Seemingly it was only the fact of the vigilante exposing the zombified minions to a double dose of fear toxin that broke Mad Hatter’s control. They were discussing ways to circumvent that problem next time when Riddler joined them to co-opt them into his scheme.

He didn’t bother with much preamble but launched into his proposition, briskly detailing the key issues he wanted their help with, and throwing in what he hoped was sufficient acknowledgment of their respective skills. As usual when he drew to a stop he was met with irritatingly blank stares and he huffed in frustration at the thought of having to explain himself a second time but _slower_.

“Let me get this straight,” Jonathan spoke before Ed could start going over it again. “You want us, to help _you_ , set Penguin up on a date?”

“Yes!” Ed grinned in relief that he’d at least got his main point across.

“And you want us to interview candidates?” Jervis queried.

“If necessary. Though there’s unlikely to be many people who are suitable. I really just want you to find someone who meets the standards and who you think Oswald will like.”

“Someone beautiful as Adonis, clever as Athena, crooked as Hermes, and with the charm of Apollo,” Jonathan recited dutifully.

“Exactly!”

“What about Maxie Zeus?” Jervis proposed. “He’s handsome and they’d have a shared interest in running criminal empires.”

“I hope you’re joking.” Ed folded his arms disapprovingly. “Zeus? That mentally deficient imbecile is nowhere _near_ Os’ level. He’s an empty headed drum making a lot of noise but having nothing sensible to say. No, no, no.”

For some reason Jonathan was smirking at him.

“Of course he’s not suitable,” he agreed. “Penguin deserves only the best, right?”

“Yes. Thank you.” Ed nodded, happy to be on the same page.

“Someone suave. Mentally dextrous. Witty. Creative. Confident.”

“Yes! Exactly. All those things. They have to be _perfect_. I knew I could count on you.” He stood up and began casting his eye speculatively around the room. “I’ll work on an escape plan for us. So long as I have your help on this?”

“Oh absolutely,” Jonathan barely restrained his laugh as Ed wandered away and Jervis slapped his arm.

“Why didn’t you tell him he’s in love with Oswald himself?”

“What? And spoil the fun?”

“I’m going to tell him,” Jervis declared stubbornly.

He immediately moved to stand only to have Jonathan grip his shoulder tightly.

“Don’t you dare.”

“But Jonathan-”

He was interrupted by an intense look that conveyed Jonathan’s seriousness.

“Which of us has the psychology degree? Listen, he’s in denial. Possibly due to childhood trauma, we don’t know. So the best thing to do is to let him come to the realisation naturally.”

Jonathan relaxed his hold as he felt Jervis slump.

“You may be right.” The frustrated expression turned pointed as he looked up at his partner. “But I can’t help but note that you can be a sadistic bastard sometimes.”

“You say the nicest things sometimes.”

The Scarecrow positively preened and Jervis rolled his eyes in fond exasperation.

“I don’t know why I love you so,” he muttered, trying to hide his adoration.

“Because I’m _your_ sadistic bastard,” Jonathan suggested in response.

And really, Jervis couldn’t argue with that.


	2. Chapter 2

Breaking out of Arkham had kept Edward occupied temporarily, along with finding a new hideout and sourcing supplies for his next grand endeavour, but eventually he got restless about his match maker scheme. Rationally he knew that Mad Hatter and Scarecrow probably needed more time to find someone suitable, and that they themselves might have had more urgent priorities upon their escape, yet he found himself thinking often of Oswald and whether or not he was lonely. So he decided to drop by the pair just to see how they were doing.

To his surprise Jonathan met him with a smile – a rare enough occasion on its own to be disturbing – and confidently declared he’d isolated the perfect individual to pair Oswald with.

“So soon?” Edward asked warily.

“Oh yes. I mean as you said yourself, the options were limited. It didn’t take much effort to investigate the most likely candidates.”

“Excellent. Good. So? Who is it?”

Jervis had joined them at this point and Jonathan was distracted briefly sharing a glance with his shorter partner before answering.

“Hhhmm? Oh. I’d rather not say.”

“What? Why not?”

Typically, Jonathan was entirely unfazed by Ed’s petulant attitude as he replied.

“This should be a private affair for Oswald and his date. He wouldn’t like to think people were speculating about it.”

Although Edward opened his mouth instinctively to object, he found the point to be valid. Oswald was an unexpectedly private person for someone so adept at being in the spotlight. He also knew that showing irritation to Scarecrow would only drive him to take further glee in denying him what he wanted.

“Can you at least confirm they meet my specifications?” he pressed, arms folding suspiciously. “Are they intelligent?”

“I’d say they were clever enough.”

“And attractive?”

Here Jonathan turned to Jervis.

“What would you say Jervis? Are they attractive?”

“I know they’ll appeal to Oswald’s taste,” he offered.

“What about charm and charisma? Will their personality appeal as much as their appearance?”

“They’re flamboyant as a flamingo,” Jervis affirmed before being interrupted by Jonathan whose patience had run out.

“Look. You asked us to find someone and we have. If you didn’t trust us to do it right, why did you ask?”

“I trust you! I just want to be sure. Oswald-”

“Deserves the best.” Jonathan concluded with a dismissive wave of his hand. “Yes. So the sooner we can move onto the set up the sooner some of us can get back to our lives.”

Edward didn’t like his haste and certainly disliked being kept in the dark. He’d rather assess this person himself – possibly in one of his riddle-laden labyrinths – but Jervis concurred.

“The sooner we can pair up Oswald with his dreamed of beau the better all round, yes?”

“Yes,” Ed agreed sulkily.

“Good,” Jonathan declared. “Now Jervis can prepare Oswald. Talk him into participating.” As Ed opened his mouth to complain, Jonathan held up a hand and spoke over him. “Edward, you’re required for setting up the venue.”

“We thought the Iceberg Lounge would be best,” Jervis put in. “A safe place for Oswald and somewhere that can be redecorated for his pleasure.”

“Which is where _you_ come in,” Jonathan took up the thread. “I will allow that… your eye for detail and… general perfectionism, will be useful.”

“Added to which you know Oswald’s taste,” Jervis agreed.

“So you can arrange everything and make sure the mood is suitable.”

“Absolutely!” Ed grinned, already both mentally picturing the perfect romantic setting and also the high probability that this would let him get a sneak peek of the chosen date. “When are we planning for?”

“I’ll speak to Oswald first,” Jervis suggested. “Find out when he’s willing to turn over his club for a private meeting. Then I’ll let you know.”

They parted briskly after that. Jervis out to visit the Penguin, Edward off to start drawing up plans that would ensure Oswald’s night was his dream romance and Jonathan back to whatever it was he did usually. Edward didn’t really pay him much mind now he’d done his part. Although the concern still niggled in his mind that this selection might not prove up to standard.

He pushed it aside with the reminder that he would have an opportunity to lie in wait, since he’d know both the time and venue, in order to provide his own character assessment.

It wasn’t long after that Jervis sent him a message to confirm Oswald had agreed to the blind date to be held the next night at 7pm. A part of Edward was surprised that he’d agreed so easily or to such a rushed arrangement. Yet perhaps Oswald was merely fitting it in to his busy schedule. Or wished to get it over with quickly. Either way, the deadline provided Ed with an even more irresistible challenge to produce something fantastic. He hoped Jervis might have name dropped his involvement and that perhaps Oswald would appreciate his effort. If so he especially wanted the décor to take his breath away.

The next day was entirely given over to preparing the Iceberg Lounge. Penguin had obviously instructed his staff to allow for his match makers to have free rein and Ed found no plan of his was meeting any resistance. He was a little disappointed Oswald wasn’t in evidence at all but realised the man was probably undergoing similar preparations upon his own person.

As the afternoon waned away, and everything that could be done had been done to make the place a palace of amour, Ed retreated to a subtly concealed staff area that allowed him to spy on events in the main room. He was pleased with what he’d managed in the time allowed, if he did say so himself, and was eager to see Oswald’s reaction when he saw it.

It was safe to say he wasn’t disappointed when Oswald finally arrived.

The man paused in the entryway to gape at the ceiling of red heart shaped balloons glittering in the reflected light from the room. A pathway to the table was lined with vases of brilliant red roses and the table itself was adorned with an antique candelabra curled into intricate flowers.

While Oswald was staring wide eyed at that display however, Edward found his own mouth drying at the vision the man himself presented. Instead of his usual trademark black and white apparel, he’d opted for a rich purple jacket with matching top hat. Underneath was a sheer silver waistcoat and an eye-catching black cravat. As he finally made his way towards his appointed seat, a strange panging feeling grew in Ed’s chest.

Once Oswald was settled Ed’s gaze turned almost fiercely to await the prospective partner, now almost absolutely certain they would be a poor match for such finery. In his mind he anticipated ripping into them if they arrived in anything less than the most expensive suit money could afford. When he recognised they were actually running late, his anger flamed higher at the affront. It was the very height of rudeness to keep Oswald waiting. An implication their time was more valuable.

Minutes ticked passed with him grinding his teeth until the gnawing realisation that they might not be coming at all occurred to him. He glanced back to Oswald and easily recognised the anxiety obvious from his fiddling with the fine cutlery.

Oswald would be absolutely crushed to be stood up. It made Ed’s blood boil to think someone would do this to him and he vowed bloody vengeance. He’d return to Scarecrow, and use any number of intricate traps on him until he revealed the name of this lowest of the low individuals, before tracking them down and putting them through exquisite torture.

But for now he had a more urgent problem. Oswald couldn’t be left wallowing in self-doubt. He needed to be reminded that his company was desirable. So he did the only logical thing he could do. Straightening his tie and adjusting his bowler, he inhaled deeply and strode towards the table himself.


	3. Chapter 3

At the sound of his approach, Oswald looked up with a luminous smile and Edward found his steps faltering. Being looked at in such a way by _Oswald_ … it made his breath come short and his heart beat too loud. Suddenly all he could focus on was that glowing face and he desperately wanted to believe that _he_ was the cause of that expression. That Oswald would feel that level of joy because of _him_.

Then the man blinked and his smile fell.

“Eddie? I thought… I was expecting… that is…”

“You were expecting a blind date,” Ed concluded for him.

“Yes.” Oswald frowned which Ed initially assumed was at his knowing the fact before Oswald continued. “Although at this stage I am beginning to conclude I have been stood up.”

Without being asked, Ed drew out the opposite chair and sat.

“That seems unlikely,” he offered. “The only reason anyone could possibly have to turn down a date with you would be a fear of their own inferiority.”

It produced a muffled laugh even as Oswald diligently folded and refolded his napkin beside his plate.

“You always know the exact right thing to say don’t you Edward?”

The reaction gave Ed a glimmer of hope and he suddenly decided to take a chance.

“Would you have any objection to me joining you for a while? Until your date arrives?”

Despite this project having been his own idea, he now found the concept of someone else sitting with Oswald, enjoying his company, infuriating. How could anyone Crane have found be worthy of this man? They couldn’t even manage to turn up on time.

“By all means.” Oswald now tilted his head up at him with a hesitant smile. “Until my date arrives.”

He turned then to gesture a server over to pour some wine.

“Would you mind if I ordered something to eat?” Ed asked as his stomach chose that moment to grumble. “I may have forgotten to eat yet today.”

A shake of the head indicated both Oswald’s amenability and his bemusement.

“How can someone be so incredibly smart and also so incompetent at basic living?”

A menu was handed across along with the vague admonition and Ed decided to let it go while he focused on what to have. Somewhat to his surprise Oswald had also started perusing the menu and he glanced over with an inquisitive look.

“They’re the ones running late,” Oswald challenged. “They shouldn’t complain if I at least have a starter.”

Ed couldn’t argue with that and minutes later they both gave orders to the waiter. After that the conversation began to flow easily. It had never been difficult for the two of them to find things to talk about. Disagreeing over the value of modernism over the classical. Laughing through various showdowns against the Bat. Challenging each other with ethical puzzles or verbal traps.

Where the time went Ed didn’t really know but suddenly they were sitting with desserts in front of them and candles long since burned down and it suddenly occurred to him that the prospective date had never showed. An anger burned in his stomach at the thought of how Oswald might have been left feeling alone and rejected if he hadn’t had the forethought to keep an eye out.

Thankful that Oswald was too intent on his chocolately treat to notice his clenched jaw, he turned his attention to his own plate before raising the topic.

“So… are you going to have words with them for bailing without even a feeble excuse?”

If Oswald didn’t he decided then he certainly would. And with Crane and Tetch too for their ineptitude. The lingering silence made him glance up again nervously, hoping he hadn’t upset his friend. It was hard to tell with Oswald merely swirling a finger thoughtfully through the swirl of sauce decorating his plate.

“That depends,” he answered slowly, raising his gaze to stare intently at Ed. “What is your excuse for this façade?”

All Ed could immediately do was gape like a fish. It caused Oswald to sigh and momentarily disregard his food.

“Really, it wasn’t hard to put together, but if you wanted to ask me out you could have just done so. Without involving Jonathan and Jervis to pretend at this whole blind date scheme.”

Edward chose to ignore the mess that most of that question would entail in answering to focus on what seemed the most important point.

“You’d have said yes?”

“Of course.” He frowned again. “Were you really so insecure that you thought I’d say no? After all the time we’ve spent together?”

“I don’t know.” Ed toyed with his own dessert now. “But to be honest…I didn’t realise how much _I_ wanted to be the one dating you until I saw you sitting here tonight.”

The low laughter brought his eyes up defensively and he was only slightly relieved by Oswald’s obviously fond look.

“So Jonathan and Jervis played you too?”

Ed offered an awkward shrug.

“I guess I underestimated the professor of psychology. I wanted him to set you up with someone _perfect_. Intelligent, verbose, culturally knowledgeable, criminally elite, handsome.” He had perked up as he talked and now smirked smugly. “He obviously realised I was the only individual to match the criteria.”

A wide hand reached over to land upon his own.

“You’re certainly the person I’d choose, even if I had my pick of the city.” His eyes lowered bashfully. “I just wasn’t sure you’d be interested that way in me.”

“How could anyone not be interested in you?” Ed brought his other hand over to encase Oswald’s. “You’re amazing. I’d be lucky to have you.”

The pink tinge lighting Oswald’s cheeks looked very becoming and Ed would have kissed them if there wasn’t such an expanse of table between them.

“When I first saw you,” Os continued softly, “walking towards the table, I thought my dream had come true. Then I chastised myself for the hope. Until you manoeuvred yourself into joining me. Then I began to understand you were simply playing it safe.” He looked up again. “But you can certainly have me. If you want.”

“I do. I want very much.” To emphasise his point Ed raising the captured hand to press a devoted kiss to the back.

“Well then.” Oswald coughed awkwardly and slid himself back to stand from the table. “Perhaps you’d be a gentleman and escort me home?”

Ed stood as well and swiftly stepped around to link their arms together.

“Certainly. Although I make no promises for when we get there,” he added teasingly.

“I was hoping that might be the case.”

And as they clambered into the waiting car, and Ed felt the undeniable grip of a hand on his backside, he resolved he’d have to send a thank you to Scarecrow and Hatter. In the morning though. For now he had his hands full.


End file.
